8. Pretty Woman (1990)

The modern-day classic date movie by which all others are measured, Pretty Woman put Julia Roberts on the map and made Roy Orbison's awesome title track a hit all over again. While it didn't invent the romantic comedy, it helped redefine the genre for a whole new generation. Sure, you've probably seen it more times than you care to admit, but this one's held up better than Richard Gere's career.